Triethylamine → HCID 57501778, compound

HRID 601543Notes

Reaction equation

HRID 601543 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:26])[N:12]([C:17]4[CH:18]=[C:19]5[C:23](=[CH:24][CH:25]=4)[NH:22][CH2:21][CH2:20]5)[CH2:13][CH2:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1.[C:27]([O:31][C:32]([N:34]1[CH2:38][CH2:37][CH:36]([C:39](O)=[O:40])[CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28].CCN(CC)CC.F[P-](F)(F)(F)(F)F.CN(C(=[N+](C)C)ON1C2=NC=CC=C2N=N1)C>C(Cl)Cl>[C:27]([O:31][C:32]([N:34]1[CH2:38][CH2:37][CH:36]([C:39]([N:22]2[C:23]3[C:19](=[CH:18][C:17]([N:12]4[CH2:13][CH2:14][C:15]5[N:16]=[C:8]([C:5]6[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=6)[S:9][C:10]=5[C:11]4=[O:26])=[CH:25][CH:24]=3)[CH2:20][CH2:21]2)=[O:40])[CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27605291-((Tert-butoxy)carbonyl)pyrrolidine-3-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57501777HCID 57501777, compound

Product 1

HCID 57501778HCID 57501778, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 2-(4-chloro-phenyl)-5-(2,3-dihydro-1H-indol-5-yl)-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one (163 mg, 0.43 mmol) in CH2Cl2 (4.0 mL) and add (±)-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (140 mg, 0.65 mmol), Et3N (0.09 mL, 0.64 mmol), and [dimethylamino-([1,2,3]triazolo[4,5-b]pyridin-3-yloxy)-methylene]-dimethyl-ammonium hexafluoro phosphate (246 mg, 0.65 mmol). Stir the solution at room temperature for 2 h. Concentrate and purify by flash chromatography, using a 8% MeOH (2N NH3)/CHCl3 as eluent, to give the title compound (231 mg, 93%). 1H NMR (400 MHz, DMSO-d6): δ 8.10 (d, 1H, J=8.8 Hz), 8.05 (d, 2H, J=8.8 Hz), 7.62 (d, 2H, J=8.3 Hz), 7.29 (s, 1H), 7.19-7.15 (m, 1H), 4.22 (t, 2H, J=8.8 Hz), 4.07 (t, 2H, J=7.0 Hz), 3.54 (t, 1H, J=8.8 Hz), 3.47-3.36 (m, 3H), 3.29 (m, 1H), 3.26 (t, 2H, J=6.2 Hz), 3.18 (t, 2H, J=8.3 Hz), 2.16 (m, 1H), 2.01 (m, 1H), 1.41 (s, 9H).

Workup

  1. concentrationConcentrate
  2. custompurify by flash chromatography

Sources & evidence

ORD record
ord-fe5a99ce7117474a8b420560fad6d23b
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

Loading…